compwpdude

bcworks,
Sorry for the very late reply. Things got busy.
Yes, I’m sure. I actually had wordpres using php mail and sending it via postfix set up as a relay server to our interanal company email sever. I was looking at /var/log/maillog to determine if an email was even generated. No emails are generated and nothing is in spam.

Anyhow, I’ve done as you suggested and have not succeeded, but i have another clue.

For starters, this was a mutli-site install and everything used to work when it was single site. But here’s what i did.

1. I duplicated the entire site on its own network, (VMWARE NAT)
2. the new site is the identical database and set of files
3. it’s now single site
4. the installation is completely containerized. (latest wordrpess and mariadb containers from docker) It’s running on podman, but that doesn’t matter.
5. the setup was verified with an initial install success, then everything from the prior site was duplicated over. (NEW site is identical to old site, but single site)

Results:
Easy WP SMPT plugin set up to do the emails.
Test emails work from a separate test email pluggin and the Easy WP SMPT plugin.
Password reset emails still fail.
So I deactivated every single pluggin except for easy wp smtp.
Same results, test work and resets fail.

Easy WP SMPT comes with a debug log. which is interesting.
1. let’s assume that the site name = internalsite <–notice no TLD
Log entry for failure = below
################
Headers: , To: user1@mycompany.com, Subject: [internalsite] Password Reset
*** Invalid address: (From): wordpress@internalsite ***
################

Background.
internalsite is not a “name” + “.com”
it’s simply name.
does wordpress expect a .com or something similar on the end of internal site?

so, i decided to see if this error was coming from our internal email server or wordpress.

I used telnet to manually send an email with the identical “from” header (as shown in debug” and the email was accepted and sent.

I’m left to assume that wordpress is generating an error. Agree?